Smartsheet: Transforming Enterprise Complexity Into Solutions-First Experiences

Redesigning core product workflows to reduce learning curve and increase feature adoption for 80,000+ enterprise users


Overview

The Challenge Smartsheet is a powerful enterprise work management platform with deep functionality, but its steep learning curve created a significant barrier between new users and the tool's full potential. Users struggled to discover features, navigate the complex interface, and understand how to apply Smartsheet's capabilities to their specific use cases—leading to low feature adoption and increased support costs.

The Solution As lead designer on the Solutions First Experiences (SFE) team, I spearheaded a comprehensive redesign of Smartsheet's core product areas—including Workspaces, Home, Global Navigation, and Search. The initiative focused on bridging the gap between novice and power users by creating contextual, intuitive pathways into the product's capabilities while maintaining the flexibility enterprise users demand.

The Impact

  • 45% reduction in time-to-first-value for new users

  • 65% increase in Workspace feature adoption within first 90 days

  • 38% improvement in search success rates across the platform

  • 4.2/5 user satisfaction rating for redesigned Home experience (up from 2.8/5)

  • Reduced support ticket volume by 28% for navigation and organization-related issues


My Role

Position: Senior UX Designer, Solutions First Experiences Team Duration: January 2022 - May 2024 (28 months) Team: Led design across multiple initiatives, collaborating with 3 Product Managers, 12 Engineers, 2 UX Researchers, Design Director, and cross-functional partners from Templates, Automation, and Core Grid teams

Responsibilities:

  • Led end-to-end UX design for Workspaces, Home, Global Navigation, and Search initiatives

  • Established cross-team collaboration frameworks to align complex multi-stakeholder product development

  • Created comprehensive product architecture maps documenting feature interconnections and ownership

  • Conducted design iterations from low-fidelity explorations through high-fidelity implementation

  • Facilitated stakeholder alignment sessions with leadership and partner teams

  • Established design review processes and best practices for the SFE team

  • Mentored junior designers on systems thinking and enterprise product design


The Problem

Background

Smartsheet had evolved into an incredibly capable enterprise platform with hundreds of features spanning project management, automation, reporting, dashboards, forms, and integrations. This depth was simultaneously its greatest strength and biggest challenge. Power users loved the flexibility—they could configure Smartsheet to solve virtually any workflow problem. But new users faced a daunting learning curve that often prevented them from ever discovering these capabilities.

The company was experiencing significant growth in enterprise accounts, but user engagement metrics revealed concerning patterns. While power users (representing roughly 15% of the user base) drove the majority of value, the remaining 85% struggled to move beyond basic spreadsheet usage. This created a disconnect between the product's potential and actual value delivered to most users.

Leadership identified this as a critical business challenge: if new users couldn't quickly understand how Smartsheet could solve their problems, they wouldn't adopt it broadly across their organizations. This limited expansion opportunities and increased churn risk in competitive enterprise deals.

User Pain Points

  • Overwhelming entry point: The home page presented users with a blank canvas and limited guidance on where to begin or what capabilities existed, creating decision paralysis and forcing users to rely on documentation or support

  • Hidden functionality: Critical features were buried in nested menus or labeled with product-specific terminology that didn't match users' mental models—for example, "Workspaces" as an organizational concept wasn't intuitive to users thinking about "projects" or "teams"

  • Poor information architecture: The global navigation had evolved into what internal teams called a "junk drawer"—miscellaneous features grouped without clear logic, making wayfinding difficult and feature discovery nearly impossible

  • Inadequate organization tools: Users managing multiple projects across teams lacked effective ways to organize their growing collections of sheets, reports, and dashboards, leading to "document chaos" at scale

  • Context switching friction: Users needed to leave their current context to search, navigate, or access important features, disrupting workflow and reducing productivity

Business Constraints

This initiative operated within significant organizational complexity:

  • Distributed ownership: Core product areas were owned by different teams with independent roadmaps, requiring extensive cross-team coordination and alignment

  • Legacy technical debt: Years of incremental feature additions created implementation constraints around what could realistically be changed without major re-architecture

  • Enterprise customer considerations: Any changes needed to support both new users and existing power users without disrupting established workflows

  • Competitive pressure: Market competition from Asana, Monday.com, and Airtable created urgency to improve onboarding and adoption

  • Resource constraints: Limited engineering bandwidth required strategic prioritization and phased rollouts

Success Criteria

We established clear metrics across multiple dimensions:

Primary:

  • Increase Workspace adoption from 22% to 50%+ of active users within 6 months

  • Reduce time-to-first-value for new users by 30%+

  • Improve search success rate (query to relevant result click) by 25%+

Secondary:

  • Achieve 4.0+ satisfaction rating for Home experience

  • Reduce navigation-related support tickets by 20%

  • Increase cross-feature usage (users engaging with 3+ major features)

Organizational:

  • Establish scalable design processes for coordinating complex multi-team initiatives

  • Create reusable frameworks for feature integration decisions


Research & Discovery

Research Methods

Given Smartsheet's large user base and established research team, I partnered closely with UX researchers to leverage multiple research streams:

  • Analytics deep-dive: Analyzed 6 months of product usage data across 80,000+ users to understand navigation patterns, feature adoption curves, drop-off points, and search behaviors

  • User interviews: Participated in 35+ interviews with users ranging from first-week novices to 5-year power users across various industries and company sizes

  • Usability testing: Conducted moderated testing sessions on current experience to identify specific friction points and mental model mismatches

  • Competitive analysis: Evaluated how similar enterprise platforms (Asana, Monday, Notion, Airtable) approached information architecture, onboarding, and organization

  • Internal stakeholder interviews: Met with customer success, support, and sales teams to understand common user struggles and feature requests

  • Support ticket analysis: Reviewed 1,000+ support tickets to identify recurring pain points and areas of confusion

Key Insights

Insight 1: The discoverability crisis

Analytics revealed that 73% of users never ventured beyond the basic grid/spreadsheet functionality, despite having access to powerful features like automation, forms, dashboards, and reports. When we interviewed users, the reason became clear: they simply didn't know these capabilities existed. The current UI provided no contextual prompts or progressive disclosure to help users discover what was possible.

One medium-sized business customer told us: "We've been using Smartsheet for two years, and I just found out last week that you can automate approval workflows. That would have saved us hundreds of hours. Why didn't anyone tell us this existed?"

This insight fundamentally shifted our approach from assuming users would explore features to designing explicit pathways that revealed capabilities contextually based on user needs.

Insight 2: Organization breaks down at scale

The "document chaos" problem emerged consistently across interviews with teams managing 20+ sheets. Users described spending significant time each day simply finding the right documents. The existing folder structure was too simplistic for complex organizational needs.

When we examined actual usage patterns, we discovered users were developing creative workarounds—creating elaborate naming conventions, using emoji in titles for visual scanning, or maintaining separate tracking sheets just to organize other sheets. These workarounds indicated a clear product gap.

The key insight: organization isn't about creating folders—it's about creating meaningful project contexts that group related work and make relationships between documents explicit.

Insight 3: Navigation has become a trust issue

Through usability testing, we observed users avoiding the global navigation entirely, relying instead on browser bookmarks, recent items, or search to access frequently used features. When asked why, users expressed a lack of confidence in finding what they needed through navigation.

Analysis of the current navigation revealed the problem: it had accumulated features over years without consistent organizational principles. Items were grouped by implementation timing rather than user mental models. Critical features were hidden in dropdown menus three levels deep.

"I know there's a way to do what I want, but I never know where to look. I usually just Google it and hope I find the right help article." — Project Manager, 500-person manufacturing company

This taught us that navigation isn't just about access—it's about building user confidence and trust in the interface.

Insight 4: The power user vs. novice false dichotomy

Initially, we framed the challenge as designing for "new users" vs. "power users." But research revealed this was a false binary. Users weren't permanently in one category—they evolved over time, and their expertise varied by feature area. Someone might be an expert with sheets but a novice with dashboards.

This led to a critical realization: we needed to design systems that scaled with user expertise through progressive disclosure and contextual guidance, rather than creating separate "beginner" and "advanced" modes.


Design Process

Mapping the Experience: Establishing Cross-Team Alignment

Before diving into design solutions, I recognized that the SFE initiative's success depended on unprecedented cross-team collaboration. The core product consisted of complex, interrelated tools owned by different teams with independent roadmaps.

My first action was creating comprehensive product architecture maps that captured:

  • All touchpoints and feature interconnections

  • Team ownership boundaries

  • Current and planned roadmap items

  • Dependency relationships

  • Potential conflict areas

I established a regular cadence of alignment meetings with partner teams, using these maps as living documents to ensure:

  • No miscommunication about ownership

  • Transparent sign-off processes

  • Early identification of downstream impacts

  • Coordinated release planning

This process became critical infrastructure for the project. As one product manager noted: "These maps finally gave us a shared language for talking about how our features intersect. We caught at least three major conflicts before they became problems."

Understanding the Global Environment

I created a second layer of documentation extrapolating how our core feature work would impact other product experiences and internal partners. This helped:

  • Identify hidden scope implications early

  • Accelerate leadership sign-off by clarifying scope expectations

  • Surface impacts to other teams' schedules and release dates

  • Create a shared source of truth across SFE and partner teams

This "systems thinking" approach became a model for how Smartsheet approached complex cross-functional initiatives going forward.


Workspaces: Designing Organizational Intelligence

Ideation & Exploration

Workspaces aimed to help users organize large document sets into understandable project structures. My early concepts explored patterns familiar from project management tools—hierarchical folders, kanban-style organization, timeline-based grouping.

Through low-fidelity paper prototypes and whiteboard sessions with internal teams, I tested various organizational paradigms:

Option A: Strict hierarchy - Folder-based organization with nested structures Option B: Tag-based flexibility - Documents could belong to multiple contexts through tagging Option C: Project-centric containers - Workspaces as distinct project environments with member permissions

User feedback from our research team revealed users needed more flexibility than strict hierarchies allowed, but not the complexity of full tag-based systems. This pointed toward project-centric containers with some hierarchical elements.



Iterative Design - Version 1

Based on requirements refinement and user input, I developed Version 1 with a deliberately simplified scope to meet initial deadlines and validate core assumptions:

  • Clean, card-based visual representation of Workspaces

  • Basic hierarchical organization within Workspaces

  • Simple member management and permissions

  • Integration with existing sheets, reports, and dashboards

The design philosophy: start simple and prove value before adding complexity. V1 launched with positive user feedback—people appreciated having any organizational tool. However, as I anticipated, users immediately requested deeper functionality.

Looking Forward: Advanced Capabilities

Anticipating user needs for greater complexity, I developed conceptual designs for future iterations:

Nested drag-and-drop organization: Allowing users to create sophisticated hierarchies within the left navigation panel, accommodating complex project structures

Document linking in automation flows: Enabling Workspaces to integrate with Smartsheet's automation engine, providing sophisticated permission management, sharing controls, and version control

Smart workspace templates: Pre-configured Workspace structures for common use cases (marketing campaigns, product launches, construction projects)

Cross-workspace relationships: Visual mapping of how documents and projects related across different Workspaces

With leadership support, I led my team in exploring how the UI could start simple but progressively reveal complexity as users' sophistication grew. This progressive disclosure approach became a guiding principle for all SFE initiatives.


Home: Creating the Front Door

The Challenge

The existing Home page was essentially a list of recent documents—functional for returning users who knew what they wanted, but providing zero value for new users exploring the platform's capabilities. Analytics showed new users spent an average of 47 seconds on Home before either searching for specific documents or leaving the platform entirely.

Leadership gave us a clear directive: transform Home into an engaging entry point that introduces both new and returning users to solutions-oriented experiences.

Design Exploration

I explored multiple approaches to the Home redesign:

Concept A: Activity-centric - Focused on recent actions, notifications, and items requiring attention Concept B: Solution-centric - Organized around common use cases with templates and pathways Concept C: Customizable dashboard - User-configurable widgets showing different information types Concept D: Hybrid intelligence - Personalized recommendations based on user behavior and organization context

Through testing with diverse user segments, the hybrid approach emerged as most promising—combining the immediacy of activity feeds with intelligent suggestions for relevant solutions.

Final Home Design

The redesigned Home experience provided:

Intelligent prioritization: Surface projects, notifications, shares, and elements requiring user attention based on contextual signals (deadlines, @mentions, recent activity)

Scannable metadata: Clear visual hierarchy showing document type, last modified, owner, and status at-a-glance without requiring clicks

Contextual onboarding: Partnership with the Templates team to show relevant starting points based on:

  • User's organization and industry

  • Stated use case during signup

  • Previous work completed

  • Collaborative patterns

Progressive feature discovery: Contextual prompts introducing advanced capabilities when users' work indicated readiness (e.g., suggesting automation after manually performing repetitive tasks)

The design balanced serving experienced users who needed quick access with new users who needed guidance and inspiration.

User Validation & Stakeholder Alignment

The Home redesign required extensive partnership with other teams—Templates, Automation, Sharing, Notifications—since we were surfacing their features prominently. This collaborative process:

  • Provided insights into surfacing tools within larger workflows

  • Required strategic alignment on business objectives

  • Demanded careful consideration of UI complexity and downstream impacts

I created comprehensive documentation and facilitated numerous alignment meetings to ensure nothing was forgotten. This process also revealed how critical global search had become for user navigation—directly informing our next initiative.


Global Navigation & Search: Solving the Wayfinding Crisis

The Navigation Audit

Working closely with the Design Director, product teams, and search specialists, I conducted a comprehensive audit of the current navigation experience. Key findings:

The "junk drawer" problem: Features were accumulated over time without consistent organizational logic, creating a confusing grab-bag of functionality

Hidden critical features: Important capabilities were buried 3-4 levels deep in dropdowns, requiring users to memorize non-intuitive paths

Unclear labeling: Product-specific terminology didn't match user mental models (e.g., "Control Center" vs. "Project Management")

Lack of customization: All users saw identical navigation regardless of their role, use case, or frequency of feature usage

Design Exploration

I explored multiple navigation paradigms through iterative design:

Condensing Ideas: I developed 15+ different layout concepts, testing variations in:

  • Visual hierarchy and grouping logic

  • Customization and personalization options

  • Feature integration approaches for scalability

  • Balance between discoverability and simplicity

Through internal testing and stakeholder feedback, patterns emerged around what worked:

  • Users valued customization to surface their frequently-used features

  • Grouping by workflow/use case was more intuitive than by feature type

  • Search needed to be more prominent and powerful

  • Future features needed clear integration methodology

Navigation Looking Forward

Through extensive conversations with product partners and leadership, I identified a forward path inspired by familiar tools like Slack:

Customizable sidebar: Allow users to pin frequently-used features and organize their navigation based on personal workflow

Smart defaults: Provide opinionated starting configurations based on user role and use case, while allowing complete customization

Unified search: Integrate search as a first-class navigation element rather than a separate tool

Progressive disclosure: Start with core features visible, with advanced capabilities revealed as users demonstrate readiness

This approach addressed the navigation problems while creating flexibility for future feature integration. While leadership decided against a complete search overhaul due to scope constraints, this design enabled search functionality at the navigation level, significantly increasing usage.


Key Design Decisions

Decision 1: Progressive Disclosure Over Separate Modes

The Problem: How do we serve both novice users who need guidance and power users who need efficiency, without creating a bifurcated experience that segregates users?

Alternatives Considered:

  • Option A: Beginner/Advanced modes - Separate UI modes users could toggle

  • Option B: Role-based interfaces - Different default experiences by user type

  • Option C: Progressive disclosure - Single interface that reveals complexity gradually based on user actions

Why This Solution: I advocated for progressive disclosure because user research showed expertise isn't binary or permanent—users evolve, and their sophistication varies by feature area. Creating separate modes would:

  • Stigmatize "beginner" mode

  • Create friction when users needed to switch

  • Require maintaining two parallel experiences

Instead, I designed interfaces that started simple but contextually revealed advanced capabilities when user behavior indicated readiness. For example:

  • Basic Workspace view shows simple folder structure

  • As users add more documents, advanced organizational tools appear

  • Automation suggestions surface after users perform repetitive manual tasks

This approach tested successfully with both novice and power users, with 94% preferring it over mode-based alternatives.

Decision 2: Workspaces as Project Containers, Not Just Folders

The Problem: Users needed better organization, but what model would be most intuitive while providing enough flexibility for diverse use cases?

Alternatives Considered:

  • Option A: Enhanced folders - Improve existing folder system with more hierarchy

  • Option B: Tag-based organization - Flexible tagging allowing documents in multiple contexts

  • Option C: Project-centric Workspaces - Dedicated containers with member management and permissions

Why This Solution: After testing all three approaches, Workspaces as project containers emerged as the winner because:

Mental model alignment: Users naturally think in terms of projects and teams, not abstract organizational schemes

Permission integration: Projects have natural permission boundaries (who should access what), which folders and tags don't address

Relationship context: Projects contain multiple related documents—sheets, reports, dashboards—and Workspaces made these relationships explicit

Scalability: Could start simple (just a container) but expand to include sophisticated features like automation integration and cross-project visibility

The trade-off was reduced flexibility compared to tags (documents could only live in one Workspace), but user testing showed 85% of use cases fit this model, and the clarity outweighed the flexibility loss.

Decision 3: Customizable Navigation as Core Architecture

The Problem: The navigation "junk drawer" needed restructuring, but how could we create an organization that worked for diverse user types and roles while accommodating future feature growth?

Alternatives Considered:

  • Option A: Fixed, opinionated navigation - Designer-determined optimal structure

  • Option B: Role-based defaults - Different navigation for different user roles

  • Option C: Fully customizable navigation - Users control what appears and where

Why This Solution: I pushed for full customization despite the engineering complexity because:

User diversity: No single navigation structure could serve all user types, industries, and workflows effectively

Adoption driver: Customization would drive engagement—users who personalized their environment showed 3x higher long-term retention in comparable products

Future-proofing: Allowed new features to be added without forcing restructuring of the entire navigation system

Learning opportunity: User customization patterns would provide data about what features matter most to different segments

The key was pairing customization with smart defaults—pre-configured navigation appropriate to user role that they could then adjust. This gave immediate value while allowing personalization.

Leadership initially resisted due to implementation complexity, but I presented data from competitors (Slack, Notion) showing customization's impact on engagement. We secured approval for a phased rollout starting with pinning/unpinning features before full reorganization.


Final Design

Integrated Solutions-First Experience

The final SFE initiative delivered a cohesive transformation of Smartsheet's core product experience across four interconnected areas:

Workspaces: Organizational Intelligence

  • Clean, card-based visual representation making projects scannable

  • Hierarchical document organization within project contexts

  • Member management and permission controls at the Workspace level

  • Integration with existing sheets, reports, dashboards, and forms

  • Foundation for future advanced capabilities (automation integration, templates, cross-project relationships)

Home: Intelligent Entry Point

  • Personalized activity feed prioritizing items needing attention

  • Smart recommendations for relevant solutions and templates

  • Contextual onboarding paths based on user role and organization

  • Scannable metadata for quick document identification

  • Progressive feature discovery prompts

Global Navigation: Customizable Wayfinding

  • Customizable sidebar allowing users to pin frequently-used features

  • Smart defaults based on role and use case

  • Integrated search as first-class navigation element

  • Clear feature grouping by workflow rather than implementation

  • Scalable architecture for future feature integration

Search: Contextual Discovery

  • Enhanced search integrated into navigation

  • Results prioritized by relevance and recent usage

  • Contextual filtering based on current workspace or project

  • Type-ahead suggestions for faster access

  • Search-to-action capabilities (e.g., "create new dashboard from search")


Design System Contributions

Cross-Team Collaboration Framework

Beyond the visual design, I established systematic processes that became organizational best practices:

Product architecture mapping: Created reusable templates for documenting feature interconnections, ownership boundaries, and dependencies—now used across Smartsheet for complex initiatives

Alignment meeting cadence: Established regular cross-team sync schedule ensuring transparent communication and early conflict identification

Review and sign-off process: Designed clear approval workflows ensuring appropriate stakeholders validated work at key milestones

FigJam collaboration workshops: Introduced collaborative conceptualization and review sessions that increased cross-functional engagement

Large-scale share-outs: Implemented regular company-wide presentations of in-progress work, fostering broader idea generation and alignment

Design Best Practices

I documented and socialized design approaches that elevated team craft:

  • Systems thinking methodology for understanding impacts across interconnected features

  • Progressive disclosure patterns for scaling interfaces with user expertise

  • Stakeholder alignment techniques for complex multi-team initiatives

  • User research integration strategies for continuous validation

Feedback Culture

Recognizing that new processes could create friction, I established mechanisms for continuous improvement:

  • Open office hours: Regular availability for partners and reports to discuss challenges

  • Team retrospectives: Structured reflection on what worked and what needed adjustment

  • Design meeting discussion time: Dedicated space for proposing process improvements

  • Anonymous feedback channels: Safe ways to surface concerns

This commitment to feedback ensured the frameworks I created remained living systems that evolved with team needs.


Results & Impact

Quantitative Results:

Adoption Metrics:

  • Workspace adoption: Increased from 22% to 58% of active users within 6 months (exceeded 50% target)

  • Multi-feature usage: Users engaging with 3+ major features increased from 31% to 52%

  • Home page engagement: Average time on Home increased from 47 seconds to 3 minutes 12 seconds

  • Search success rate: Improved from 51% to 73% (query to relevant result click)

Efficiency Gains:

  • Time-to-first-value: Reduced by 45% for new users (from 8.7 days to 4.8 days average)

  • Document organization time: Project managers reported 35% reduction in time spent finding and organizing documents

  • Navigation efficiency: Users accessed frequently-used features 52% faster through customizable sidebar

Business Impact:

  • Support ticket reduction: Navigation and organization-related tickets decreased 28%

  • User satisfaction: Home experience rating improved from 2.8/5 to 4.2/5

  • Feature discovery: 40% increase in users trying advanced features (automation, dashboards, reports) within first 90 days

  • Enterprise expansion: Contributed to 15% increase in seats per enterprise account (users brought more teammates onto platform)

Qualitative Feedback:

"The new Home page actually makes sense now. I can see what needs my attention and discover features I didn't know existed. It's like Smartsheet finally understands how I work." — Marketing Operations Manager, Fortune 500 retail company

"Workspaces changed everything for our team. We went from 50+ scattered sheets to organized project spaces where everything related actually lives together. Our project managers are spending time managing projects instead of hunting for documents." — IT Director, 200-person consulting firm

"I've been using Smartsheet for three years, and the navigation improvements finally make it feel like a modern tool. Being able to customize what I see means I'm not wading through features I never use." — Construction Project Manager, 500-person general contractor

Adoption & Behavioral Changes:

Within 6 months of rollout:

  • 87% of active users engaged with at least one SFE feature (Workspaces, redesigned Home, or customized navigation)

  • Workspaces became sticky: 82% of users who created a Workspace continued using it actively after 30 days

  • Customization drove engagement: Users who customized their navigation showed 2.8x higher weekly active usage

  • Cross-feature discovery: Users who adopted Workspaces were 3.5x more likely to try automation features—evidence that better organization revealed capability awareness

The most significant indicator of success: organic feature adoption without marketing push. Users discovered and adopted these capabilities through the product experience itself, validating the "solutions-first" design approach.


Reflections & Learnings

What Worked Well:

Systems thinking approach: Taking time upfront to map the complex product architecture and establish cross-team alignment processes paid enormous dividends. By identifying dependencies and potential conflicts early, we avoided at least four major scope collisions that would have significantly delayed launches. This approach became a model for how Smartsheet tackles complex initiatives.

Progressive disclosure philosophy: Designing interfaces that scaled with user expertise rather than creating separate beginner/advanced modes proved successful across all our initiatives. User testing consistently showed this approach served both novice and power users effectively without creating artificial boundaries.

Collaborative design process: Rather than designing in isolation, I involved product managers, engineers, and partner teams throughout ideation and iteration. This created shared ownership and surfaced implementation constraints early, resulting in designs that were both ambitious and buildable.

Establishing process infrastructure: The documentation, review frameworks, and collaboration rituals I created became organizational assets beyond just this initiative. Multiple teams have since adopted and adapted these processes for their own complex projects.

Challenges Overcome:

Navigating organizational complexity: Coordinating across multiple teams with independent roadmaps was perhaps the biggest challenge. Early attempts at alignment meetings were chaotic and unproductive. I addressed this by:

  • Creating shared visual artifacts (architecture maps) that gave teams common language

  • Establishing clear decision-making frameworks to prevent endless debates

  • Building trust through transparency about scope and constraints

  • Celebrating team wins and recognizing partner contributions publicly

Balancing user diversity: Serving novices and power users simultaneously seemed impossible initially. The breakthrough came from reframing the problem—rather than thinking about user types, thinking about user evolution. This mental shift unlocked the progressive disclosure approach that worked for everyone.

Managing scope creep: With so many features interconnected, every design decision threatened to expand scope exponentially. I managed this by:

  • Clearly defining V1 vs. future iterations upfront

  • Using the "MVP that validates core assumptions" framing to keep focus

  • Documenting "parking lot" ideas for future consideration

  • Regularly reinforcing the phased rollout strategy with stakeholders

What I'd Do Differently:

Earlier quantitative validation: While we conducted extensive qualitative research, I wish we'd established more rigorous A/B testing infrastructure earlier in the process. We ended up validating designs primarily through moderated testing, which gave rich insights but limited statistical confidence. For a product serving 80,000+ users, earlier quantitative validation would have accelerated some decision-making.

More aggressive prototype testing: We tested high-fidelity prototypes, but I should have pushed for earlier interactive prototype testing with actual customer data. Some interaction patterns that seemed intuitive in prototype revealed friction only after implementation with real-world document quantities and complexity.

Deeper mobile consideration: Our designs prioritized desktop experience, with mobile as secondary consideration. Given that 30% of Smartsheet usage happens on mobile devices, I should have advocated for mobile-first thinking on certain features, particularly around quick navigation and status updates.

Future Opportunities:

The SFE initiative laid groundwork for exciting next-phase possibilities:

AI-powered assistance: With better information architecture and user behavior data, we can now introduce intelligent assistance—proactively suggesting solutions, automating repetitive tasks, and predicting user needs

Workspace automation: Building on the Workspace foundation, we can create sophisticated automation flows that span multiple documents and orchestrate complex workflows

Cross-workspace intelligence: Enabling visibility and relationships between Workspaces would help organizations understand dependencies and impacts across their entire work portfolio

Advanced personalization: Using machine learning on customization patterns to automatically optimize navigation and Home experiences for individual users

Template marketplace: Building on the template integration in Home, creating a robust ecosystem where users can share and discover pre-configured Workspace solutions for specific use cases

The most exciting aspect: we've established the architectural foundation and design patterns to support these advanced capabilities without requiring another fundamental redesign.


Related Work

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